There are two methods users can ask questions to the candidates in a moderator elections:

They can comment on the nomination

They can ask a question in the town hall chat.

The comment system has the disadvantages that it is nearly invisible once the nomination phase is over, that it is unorganized and often filled with tangential comments and that candidates can easily avoid it by nominating shortly before the deadline.

The town hall chat is a very good idea in principle, but I don't think that using chat for this is ideal. The huge main problem is that using chat severely limits the number of users that can actively participate. You have to be present at the exact time, which is often difficult especially when different timezones come into play. Of course users can ask someone else to put forth a specific question and read the transcript later, but that is not obvious to most users. The timing is also less than ideal, as the exact time and date can only be arranged after the nomination is finished, which puts the town hall rather late into the election cycle.

Instead of a real-time chat I would propose that users can submit questions during the nomination phase, and that all candidates then get the opportunity to answer those questions whenever they have time. This would eliminate the need to find a date and time for the chat event, which is usually rather difficult due to timezone differences.

It might also make sense to allow voting on the questions themselves, and give an easy way to see the answers of the candidates to the most upvoted questions. It might also be necessary to be able to close non-constructive questions. The idea is to give voters more chances to ask the candidates questions, and to make the results more easily available and more obvious than the current town hall transcripts.

2 Answers
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I was a candidate in a moderator election this summer. Even though the timing of our chat was challenging for me, I found enormous benefit in the real-time nature of it. It gave voters a chance to see candidates' first instincts rather than polished responses. Yes, for serious actions we hope mods will take time to deliberate and confer, but knowing people's tendencies still seems valuable. (Note: I didn't have time to read others' responses during the chat; the questions were coming too quickly. I read the transcript afterwards just like (I think) all the other candidates. So we weren't (much) reacting to each other.)

We had one candidate who could not attend the chat. We knew this in advance and discussed on meta with SE reps, who told us he could enter the chat room later that day and answer the questions. He did and his responses were included in the digest same as everyone else's.

I don't have the data on this any more, but I think way more people read the transcript than attended the chat. There was also an offer to ask questions on behalf of people who couldn't be there.

So I think between these mechanisms and the fact that nothing prevents questions of candidates on meta during an election, the current system works. I don't believe I am saying that just because I was elected (so you could say it worked for me); I think it worked for our community.

Yeah, this is really the key point for me. While not everyone always gets to attend the live session, so far it's seemed to work out quite well. As a result I don't really see a problem that needs "fixing", and I'd also worry about the candidates being overburdened with questions in a long-running, unrestricted setup like the one the question proposes.
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Tim StoneDec 20 '12 at 15:43

I'd slightly argue that "asynchronous Q&A" is partially how the Town Hall goes at the moment. At least, based on what I always end up explaining to folks as I schedule things. But I know that what you're looking for is slightly different than how this works anyway.

The process exists primarily to give organization and structure to the questioning. Rarely do all the askers and answerers have full capability to attend the live event and I've always explained the alternative. Askers who can't attend are always free to leave me questions to ask during the event, answerers who can't attend are always free to show up at their earliest convenience to answer what was asked.

So in practice, it's mostly an asynchronous Q&A and the live event is sort of a ritual to just carry out the general gist. "Active" participation just means you showed up during the allotted time, there's no bonus or advantage to being present at the event. It's all about the presentation and atmosphere, the data persists. I like this ritual over a timeless Q&A session, for two big reasons.

First, the time makes it so that questions are asked, by giving a structured point for people to come. It avoids for both the askers and the candidates from just thinking "I will get around to it some time", which notoriously causes people to forget about doing it at all. Thus people can prepare for this and organize their questions all at once, rather than giving light thought to it over the whole election period. Likewise it gives the candidates a concrete time to expect things so they know they can answer what is asked. It's all about having exactly the time for the people to "get around to it".

Second, the time period serves as a limiter, to avoid overwhelming the candidates with too many questions and the voters with too much information. Readers will know when they can stop reading and make a decision, which is the entire point of the Q&A is to assist in making a decision. If there is no limit, they then hesitate whenever they could make a decision, thinking "Wait, what if someone asks a new question?". Checking in to see new developments is always crucial to making an informed decision, but having some comfort to relax on that front is nice as well.

As for visibility of the event... I think the digest is pretty visible. It's a big meta question with a lot of responses on it, and it's a fresh new one when it is posted with all the actual content from the proceedings. This gives it a lot of oomph to be seen on Meta, even on highly active sites. I'd think that doing a free-form Q&A like people did back in the early elections (and sometimes still do) would be just as visible at the end, but not really more visible.

On thinking a bit more about it I'm probably overcomplicating things. But there are some aspects that are not optimal, my main concern is that the timing is not so good especially when the primary is skipped, and I would like to have the answers by the candidates available from a link on the election page.
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Mad ScientistDec 20 '12 at 17:53

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@Mad I could add "Make a link to the digest from the election page" to the list of "Things that should be done".
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Grace Note♦Dec 20 '12 at 18:03